--- title: "Nef reaction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/nef-reaction/ description: "Nef reaction template: NaOH turns 2-nitropropane into its nitronate; in cold strong acid it is protonated twice on oxygen, water adds to carbon and loss of…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Nef reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Nef reaction template ![Nef reaction template: NaOH turns 2-nitropropane into its nitronate; in cold strong acid it is protonated twice on oxygen, water adds to carbon and loss of water and HNO gives acetone.](https://www.moldraw.com/templates/nef-reaction.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). NaOH turns 2-nitropropane into its nitronate; in cold strong acid it is protonated twice on oxygen, water adds to carbon and loss of water and HNO gives acetone. ## Mechanism step by step A nitronate salt poured into strong acid gives a ketone or aldehyde and N₂O 1. **Nitronate formation** – Hydroxide removes the acidic α-H (pKa ≈ 8 in water): the nitronate anion 2. **O-Protonation** – In strong acid the nitronate takes a proton on oxygen: the nitronic acid (aci-nitro form) 3. **Second protonation** – A second proton on oxygen gives a very electrophilic iminium-like carbon 4. **Water adds to carbon** – Water attacks the C=N⁺ carbon 5. **Proton transfers, − H₂O** – Loss of a proton and of water from N(OH)₂ gives a 1-nitroso alcohol 6. **Fragmentation** – Loss of the O–H proton breaks the C–N bond: acetone and nitroxyl (HNO), which gives N₂O + H₂O ## Key points - Primary nitroalkanes give aldehydes, secondary give ketones; tertiary nitroalkanes have no α-H, form no nitronate and do not react. - The nitronate must go into strong acid (pH < 1); in weaker acid oximes and other by-products form. - Nitroalkanes are acyl anion equivalents (umpolung): a Henry or Michael reaction followed by the Nef reaction makes carbonyl compounds. - Milder variants: oxidative (KMnO₄, Oxone, O₃ on the nitronate) and reductive (TiCl₃, which goes through the oxime). Drawn with 101 atoms, 19 arrows, 10 shapes – every one editable in MolDraw. ## Sources - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 16](https://openlibrary.org/isbn/9781119371809) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Nef reaction template free? You can preview the Nef reaction template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Nef reaction template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### Which name reactions are included? 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